I never expected for Mr. Jackson to get Mr. Sherwood fired. I should never have said anything about Mr. Sherwood coming on to me. Even with that said, the reality is Mr. Jackson would have found out eventually. He seemed to have eyes and ears everywhere and nothing slipped by him.
I also never expected that Mr. Jackson would be so possessive of me, calling me “his pussy boy” and calling my butt hole “his pussy” every time we met. To be honest, I was scared of him when he threatened me, when he said if he caught me even looking at another man he would destroy me. On the other hand, having a man like Mr. Jackson covet me was such a turn on, and he was carrying a cock so big I would never dream of another one. He’s more than enough for me, all the man I need right now.
I wondered who would be our new principal. Now doubt it would be someone Mr. Jackson would have approved and fully vetted.
Not even a week after Mr. Sherwood was sent packing, the position was filled. A man named Mr. Dean Young. Damn, if he wasn’t an older version of me. I’m a short statured, toned, blonde twink with blue eyes and a smooth body. Mr. Young had a wrinkle or two around the eyes, and a thick dirty blonde handlebar mustache, but he could have passed for my older brother. An inch or two taller than me, with the most engaging smile I’d ever seen. Shit, how was I going to hide my attraction to this man from Mr. Jackson?
On the very same day Mr. Young started his tenure at the school, I went to visit Mr. Jackson for my daily dick feeding. I was down on my knees, on the dirty linoleum floor, when Mr. Jackson decided to share with me exactly how Mr. Young landed the job.
While his hand was over my head loosely guiding my throat over his cock, I heard the entire story.
“You know how Young got this job, don’t you pussy boy? He got it because he passed my test. The school board knew better than to place a principal at this school without my sign off. I had ‘em here two days ago, right where you are now. I need a new harem of cocksuckers to take care of this dick since I had to transfer the last group out of here. Let me tell you, pussy boy, Young can sure suck dick, but he’s gonna need some practice, just like you did when you first got here. I have full confidence he’ll be just as good as you in no time.”
“Mmm hmmm”, I continued to enjoy this huge cock deep in my throat and wanted to signal to Mr. Jackson that I was, indeed, listening.
“But that’s not all, pussy boy. You know I had to see if that ass had any potential. A little variety does a man good. You know what that cocksucker had the nerve to say to me?”
“Mmm mmm”, I mumbled.
“He said he doesn’t take dick up the ass! I asked just how badly he wanted this job, and if he did he’d better change his mind.”
“Mmmmm”, I really couldn’t form words with a mouthful of manmeat.
“It was so easy. He pulled his pants down and showed me his ass right away. He had a really great ass, pert and juicy, just like yours, but it had hair all over it. I told him I don’t like that. I like my pussy boys smooth.”
“Mmm hmmm”
“He looked at me like some kind of idiot. I had to explain to him what’s what. I said to him that if he wanted this job I was gonna be fucking his ass on the regular and he’d best see to it that his ass be smooth as a porpoise.”
“Mmm hmmm”, when I tried to lift off, Mr. Jackson pulled my head back down.
“Where you goin’ pussy boy? I’m not done with you yet, and I haven’t finished telling you the story.
“Mmmk”, I said.
“Where was I. Oh yeah, I remember now. You should have seen the look on his face. Then he said he’d never had a dick up his ass before and nobody told him that this would be part of the job. I told him it was under the category of “other duties as assigned”, and it would very much be a condition of his employment.”
“Mmmmm mmmmm”, Mr. Jackson’s cock was stiffening up for me now. I think he was getting so close.
“He asked if I was going to fuck him right then. I told him not yet, not until he accepted the job and got that ass the way I like it.”
Mr. Jackson was now taking an active role in his blowjob, thrusting cock into my mouth.
“And you know what pussy boy? Just yesterday when he signed his contract I railed him right over his desk. You know I had to welcome him and break him in. That was a very tight pussy, I’m telling you. He shaved his pussy, too, just like I told ‘em to. That boy was whimpering the entire time, not like you who can take a good pussy pounding. But don’t you worry, I’ll get him there. I have big plans for your new boss.”
Just then, Mr. Jackson stopped talking and drilled my throat until he fed me his load. It was almost time for me to get back to class.
When I got off my knees, Mr. Jackson had a look of satisfaction on his face. He tucked his now flaccid penis into his pants and zipped up.
“I know what you’re thinking pussy boy.”
“You do, Sir?”
“Oh yeah, you’re thinking you don’t wanna share my big cock with another bottom, and that’s natural. I wouldn’t want to share either if I was a pussy boy faggot like you, but there’s more than enough cock for the both of you. There’s no need to worry about that.”
“Thank you, Mr. Jackson.
“No problem pussy boy. Check in with me later. Young has some meetings with the school board so I’m gonna need that sweet pussy of yours to unload in.”
“Yes, Mr. Jackson, Sir.”
“Such a respectful pussy boy. Makes me chub every time I hear it.”
My afternoon classes went well. The students seemed very engaged and interested which always makes the time fly by.
But at the very end of class, one of my male students stunned me with a question.
“Mr. Prince, why do you spend so much time in Mr. Jackson’s supply room?”
“Excuse me, Sean?”
“A few of us have seen you going there at least twice a day. I’m just curious.”
“Sean, that’s none of your business. Just focus on your grades and not on me and what I’m doing.”
“Mr. Prince, why are you blushing?”, another student, Jordan asked.
“Jordan, stop causing trouble. That’s enough. Class dismissed. Make sure you do your reading because tomorrow I’m going to test you on it.”
After a collective groan from the class they all filed out without anymore questions about my whereabouts. Still, I didn’t like it.
I waited several more minutes to be sure all the students would have left for the day before going to see Mr. Jackson.
“Hey pussy boy, why are you so late?”
“Sorry Sir, just wanted to make sure my students were gone for the day. They’ve seen me coming in and out of here.”
“I wouldn’t worry about it pussy boy. Ain’t nothing gonna happen to you. I’m the only one who you need to be worried about.”
“Thank you, Mr. Jackson, Sir.”
“Well, what are you doing pussy boy? I can’t get to my pussy with your clothes on!”
“Yes Mr. Jackson, Sir.”
I pulled my khakis down below my hips and then my briefs, exposing my flesh to Mr. Jackson.
“There she is. My favorite sex toy. Bend over and let me see it properly.”
I assumed the position of hands on ankles.
Mr. Jackson’s calloused hands massaged my smooth glutes.
“Mmmm mmmm, pussy boy. You keep my pussy in such fine shape. You wanna warm it up for me? Wet your finger and let me see you play with it.”
This was a new request and a bit humiliating. I’ve played with my asshole when I’ve been alone, but never in front of another man. I was in no position to argue. I wet the index finger of my left hand and brought it to my pucker.
Mr. Jackson actually pushed it inside.
“Don’t be bashful pussy boy. I wanna see it go in and out, swirl it around, get it perfect for my big fat dick.”
I heard Mr. Jackson unzip behind me. He was jerking his meat while watching me finger myself. He actually spit in my hole so I’d have more lubrication.
“That’s a good pussy boy. That looks so hot. I’m gonna own that pussy any minute.”
After just another minute of playing with myself, Mr. Jackson swatted my hand away and pushed his cock inside me.
“Fuck yes! That’s my pussy! I was looking forward to this all day.”
Mr. Jackson’s hands grabbed a handful of ass flesh and proceeded to drive his erection in and out of my opening hole. I could feel it loosening with every single stroke, acclimating to the invasion.
I was startled when Mr. Jackson struck me hard with an open hand.
“Ride my cock, faggot! I wanna see that pussy bounce!”
I placed my hands on the floor for a better position and glided my hips forward and back, over and over again, faster and faster as Mr. Jackson kept slapping me and encouraging me to keep going.
“Feels so good pussy boy. Watching you work that pussy up and down my cock is fucking hot! Ride it, faggot!”
I was really enjoying the ride to be completely honest. I found just the right angle to maximize my own pleasure. I began to moan like a $2 whore.
“You gonna squirt for me pussy boy? Go on, fuck your pussy on my cock! Let me see you cum for me pussy boy!”
“Ohhh yesss! Ohhhhh yesss!”, I moaned like the girls I’d seen in straight porn movies. Without laying a finger on my little dick, streaks of white cum painted the floor. I was out of breath and my ears were ringing. My hole had tightened like a vice around that thick and long cock meat, clenching on for dear life.
“Wow, that pussy sure did squirt! Look at that! Now it’s my turn to cum pussy boy faggot!”
Mr. Jackson grabbed onto my shoulders and his hands pushed me backwards so I was completely impaled on every millimeter of dick he had on offer. Keeping the pressure on my shoulders, his ass did all the work, pulling back and thrusting in repeatedly, like he was drilling for oil.
“Mmmm mmmm mmmm, this is some prime pussy you got! My cock loves fucking this pussy. You ready for my load, pussy boy? I don’t really care if you’re not, it’s my pussy and I’m gonna breed it anyway. Fuck! Ohhh here it cums pussy boy! Brace yourself! I’m gonna flood my pussy! Ohhhh fuuuckk! Oh yeah! Ohhhhh fuck yeah!”
I took Mr. Jackson’s seed like a champ. Without prompting, I cleaned off his shaft and made sure he was completely satisfied.
“You made a mess down there, pussy boy. You gotta clean it up.”
“Yes, Mr. Jackson, Sir.”
I looked around for a rag or a mop.
“Pussy boy! What are you doing? I said you gotta clean up your mess!”
“I’m looking for a mop or a rag, Mr. Jackson, Sir.”
“What makes you think I’m gonna let you use my supplies to clean up your pussy juice?”
“Sir?”
“Sometimes I just don’t get how dense you are pussy boy! You have a fucking degree but you ain’t so bright are ya? Let me spell it out for you. Get on your fucking hands and knees and use your mouth to clean up your pussy juice. Now!”
I was trembling in my shoes.
“Yes Mr. Jackson, Sir.”
I darted my tongue in a large pool of jizz and tasted the cool liquid. I’d eaten my own load before, but never off the floor like this.
“I don’t have all day pussy boy. Clean it up!”
Mr. Jackson pushed his boot down on my the back of my head. Suddenly, I lapped it all up and the floor shined like new. My face was smothered in a coating of shiny jizz.
“Good job, pussy boy. See you tomorrow.”
Just as I was walking out of Mr. Jackson’s closet with that cummy, wet, face, I bumped into Mr. Young.
“Hello Sir”, I said.
“Were you just in with Jackson?”
“I was, yes Sir.”
“You must be the other one.”
“The other one, Sir?”
“You’re definitely the other one. Jackson mentioned something about having a very respectful and young pussy boy. It has to be you, well, and that mess all over your face also gave me a clue.”
I was embarrassed.
“Nothing to be ashamed of young man. Mr. Jackson is a demanding man. If I don’t surrender my ass to him, I’m out of a job. He called me his “other pussy boy”. Don’t worry, your secret is safe with me.”
“Thank you, Mr. Young, Sir.”
“Can I ask you a question?”
“Sure, Mr. Young.”
“What happened to the last school principal? Why did he lose his job?”
“Mr. Sherwood made Mr. Jackson mad when he came onto me.”
“That’s it? He never touched you?”
“No, but he wanted to.”
“And Mr. Jackson got him fired just for that?”
“Yes. Mr. Jackson doesn’t want me to be with anyone else but him. He calls me his pussy boy every single day, Sir.”
“Well, I’m glad you told me or I would have made the same mistake. You’re a good looking young man.”
“Thank you, Sir.”
Just then Mr. Jackson emerged from his office with a huge smile.
“Hello Mr. Jackson”, Mr. Young said.
“’Young, you coming to see me or not? I got things to do.”
Mr. Young and Mr. Jackson left me right there speechless while the two of them retreated back into Mr. Jackson’s closet.
I couldn’t believe Mr. Jackson had it in him to go again after just finishing with me, but he’s a man full of surprises.
Just when I thought I was off the hook and done with Mr. Jackson, he poked his head out the door.
“Hey pussy boy!”
“Yes, Mr. Jackson, Sir?”
“Get your ass back in here!”
When I walked back in, Mr. Young was bent over the back of Mr. Jackson’s desk chair and his bubble butt was exposed.
“That’s a fine looking pussy, don’t you think so?”, he asked me.
“Yes Mr. Jackson, Sir.”
“You’re too far away, get a really good look at it. On your knees, get right behind it and look at that pussy up close.”
“Excuse me, Sir?”
“Pussy boy! Did you not hear me? I said get on your fuckin’ knees and look at your boss’s pussy ass up close!”
“Yes Mr Jackson, Sir.”
I was so nervous, some of Mr. Jackson’s seed gushed right out of my asshole!”
“Put your hands on it!”
“Yes Mr. Jackson Sir.”
It was nice and round, two perfect fuzzless peaches. I wondered what Mr. Young was thinking as he was bent over that chair with my hands on his ass.
“Spread ‘em pussy boy!”
I pulled both hands out to open Mr. Young’s ass crack.
“Now put your face in there, pussy boy. Get that pussy nice and wet for me.”
“But, Mr. Jackson, I..!”
Mr. Jackson pushed the back of my head right up in it.
“Yeah, that’s it. Get your tongue in there. I got my pussy boy eating out my new pussy for me. Don’t you fuckin’ dare stop until I tell you to stop. You just stay right there and do as your told pussy boy!”
Mr. Jackson walked to the front of the chair and pulled his dick out.
“Open!”
Mr. Jackson shoved his cock inside Mr. Young’s open mouth
“Do you know where this cock has been? You wanna know why it tastes like pussy? I’m happy to tell ya’”, he started to say as his cock was being pleasured.
“Watch your fuckin’ teeth or I’ll knock ‘em out!”
A pause…
“Now you’re gettin’ it cocksucker. I’d have my pussy boy tell you himself where my cock has been but he’s a little busy right now, aren’t you pussy boy?”
“Mmm hmmm”, I mumbled.
“This dick was up my pussy boy’s ass not even fifteen minutes ago. I used my pussy good, fed it a nice full load. I know, you must be thinkin’ I ain’t got no more for you. Don’t despair, see how hard my cock is in your mouth? It’s gonna feel even better up your ass. I’m gonna pull my dick outta ya’ mouth and shove right up ya’ pussy hole.”
Mr. Jackson stepped back over to where I was and shoved me away.
My face was dripping wet.
Mr. Jackson used my spit for lube and for the first time I heard Mr. Young cry out in a burst of agony.
“You can go now pussy boy. You did your job.”
Poor Mr. Young. I didn’t know if I should wait for him to see if he was alright or not, but I really just wanted to go home so I could shower and have some dinner.
My face was still a mess and as I was walking over to the teacher’s men’s room to wash my face, my students Sean and Jordan were walking towards me.
I tried to wipe my face with my sleeve, but not on time.
“Why is your face all wet, Mr. Prince?”
“Boys, what are you doing here?”
“Does that matter? What is that all over your face? It looks like you were eating pussy, Mr. Prince!”
“Sean, I will not have you speaking so disrespectfully to me! I am your teacher! Tomorrow you both have detention!”
“What did I do, Mr. Prince?”
“You’re his accomplice Jordan. That makes you guilty as far as I’m concerned.”
I stormed into the bathroom to finally wash my face. I then went back up to my classroom just to grab my coat and some things to take home.
On the way back out to the parking lot, there was Mr. Young. He looked so upset.
“Are you ok, Mr. Young?”, I asked.
“No, I’m not ok! Jackson’s cock is so huge it felt like he was ripping me in half. I don’t know how you do it.”
“I’m just used to it. It hurt me too in the beginning, but now I can’t get enough of it.”
“You mean you like it?”
“I love it. I need it, and I try to get it every single day. Mr. Jackson has me addicted to his cock.”
“That’s unbelievable. After he finished fucking me, he asked if I found you attractive. I said I did, innocently because you’re a very sexy young man. you know what he said?”
“No, what did he say?”
“He said that’s my pussy and he’d see to it that I’d never have it. He said Sherman wanted to fuck you and he would never allow anyone else in his pussy.”
“Oh my god! He’s so possessive of me, it’s crazy.”
“Yeah, he is. You know what he did? He put a chastity cage on my dick and held the key! He said that would keep me from getting any ideas and would keep his pussy pure. The man is insane!”
“Are you serious?”
Mr. Young placed my hand over his crotch and I felt something hard, like metal.
“I’m so sorry, Mr. Young.”
“If I wasn’t buried in a mountain of student debt and other bills, I’d quit this job, but I need it. I’m just going to have to live with this for now. I’m going home, I need a drink.”
Things have really gotten off the rails with Mr. Jackson. I decided I needed to figure a way out of this. I wasn’t sure I wanted to be his pussy boy any more.
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